Methyl 2-(5-amino-2-methylphenyl)acetate → 2-(5-Amino-2-methylphenyl)ethanol

HRID 2067910Notes

Reaction equation

HRID 2067910 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:6]=1[CH3:12]>C1COCC1>[NH2:11][C:9]1[CH:8]=[CH:7][C:6]([CH3:12])=[C:5]([CH2:4][CH2:3][OH:2])[CH:10]=1

Participants

3

Reactant 1

HCID 46741401Methyl 2-(5-amino-2-methylphenyl)acetate

Product 1

HCID 585422572-(5-Amino-2-methylphenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-amino-2-methyl-phenyl)-acetic acid methyl ester 49 (1.4 mmol) in THF (7 mL) at 0° C. is added 1M lithium aluminum hydride THF solution (1.4 mmol). The reaction is stirred at rt for 6 h and subsequently quenched with ice water and partitioned with ethyl acetate. The organic layer is washed with brine, dried over magnesium sulfate, filtered and reduced to dryness to yield 2-(5-amino-2-methylphenyl)ethanol 50 as tan crystalline solid, which is used without further purification.

Workup

  1. customsubsequently quenched with ice water
  2. custompartitioned with ethyl acetate
  3. washThe organic layer is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-842eae6efa13400ea723c4b238c8cd4c
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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